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We found this sort of enclave of graffiti buildings during our first walk around Havana. It felt like all the street art had merged in one area.

Photo: Courtesy of Natalie Joos

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I celebrated my birthday on the trip, and I got a Minnie Mouse headband that lights up when you flip a switch. And what better place to wear it than under the water at the pool at our guest house?

Photo: Courtesy of Natalie Joos

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When we first pulled up to the guest houses (what they call casas particulares) we stayed in our cab, we all wanted to turn back and run because the street was abominable and the building was crooked. But when we entered on the 14th floor, it was like a tropical paradise with marble floors, exotic plants, fifties furniture, and this amazing pool.

Photo: Courtesy of Natalie Joos

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Bikes parked on Playa Ancon.

Photo: Courtesy of Natalie Joos

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A visit to the town of Trinidad is an exercise in time travel. It’s like the clocks stopped ticking in 1850—a horse and carriage is the main form of transportation, and the colors are more vibrant than in Havana.

Photo: Courtesy of Natalie Joos

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A lot of Cubans have great fashion sense, but this guy had actual swag. He walked around town in a cool outfit waiting to be photographed so he could charge a dollar. It’s street style, but way more lucrative.

Photo: Courtesy of Natalie Joos

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The best thing about Havana? The colors!

Photo: Courtesy of Natalie Joos

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The second best thing? The 1950s cars!

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With the East Coast still trapped in winter’s unrelenting, frigid grasp and summer still five long months away, it seems the perfect moment to relive happier (and often warmer) times. Thankfully, a few of our favorite women—including Marchesa’s Keren Craig, Natalie Joos, Leslie Kirchhoff, and Chloe Perrin—stepped up, sending along their holiday vacation pictures, which take us away from our grim workaday desks and throw us gleefully into an assortment of balmy Mexican resorts, hidden waterfalls, and cozy mountain cabins. If you haven’t yet booked your plane tickets for spring break, consider this your visual reminder.